After My First Makeover

Continuation of my "First Makeover" story. Tim had met me in my hotel after my makeover and I ended up giving him my first blowjob (so amazing). The story continues after he left my room.

I went to the bathroom and took off all my makeup and wig, the makeup removal was quite a chore as Val used much heavier makeup than I ever have in the past.

I was still in a daze from the whole day, nails getting done, full makeover, and especially the time spent with Tim. I had actually touched a cock, put it in my mouth and let a guy cum in my mouth. I felt like I had taken a big step and it was something that changed me from a straight guy (that crossdresses) to something else, maybe bi, maybe trans or not really sure. Then I still had the thought of seeing Tim tomorrow and what that might entail. These thoughts were swirling around my head as I went to bed.

The morning came quickly and I was up pretty early as I heard my phone buzzing from a text. It was Tim and he asked me if I was willing to go to dinner with him tonight. I got some butterflies in my stomach but they were good ones and I immediately went into girl mode thinking that I would need to get a new outfit and some cute heels that were easier to walk in, and if I was going to be in public, I wanted a better wig and some more makeup. I texted Tim back and let him know I would be happy to have dinner with him, but also told him I wanted to be a little discrete since I was not very comfortable being out in public. He said great and had a place he thought would be perfect, not upscale but nice and in a "friendlier" area of town. We set a time for 7pm for him to pick me up.

I looked at the clock and it was just past 9, and I started to mentally go through what I wanted to get done today and organized what to do first. I thought the wig might be the hardest to find so I started with that and found a couple of places that were nearby to tryout.

I cleaned myself up a bit and shaved my face again, then did some light makeup, and put on some clip-on earrings. I styled my own hair a bit and then I got on my white jeans, flip flops and cute tight black top which I wore before my mani pedi. I was trying to look as feminine as possible without a wig. After a drive-up coffee, I got to the nearest wig store and went inside. A nice lady came over and asked if I needed any help. I told her the truth that I wanted a wig to make me look feminine and wanted real human hair in a dark blonde and auburn colors. She was really nice and had me sit while she got out many wigs to try. I tried on about 10 different ones and settled on a blonde long one that parted on the side with darker highlights; and a medium length auburn one that parted in the middle and had some nice wavy body to it. I loved them so much and was so excited to be able to wear one tonight. I now had to think about what to wear tonight so went to the mall to shop.

I had a thought of a look I wanted to have for tonight....I wanted to have a cream or white top, with a cute cream sweater, and a tan (maybe leather or suede) skirt and some mid heel booties. I would also wear some sheer tights with it or maybe nude fishnets. I really love hose and I know it would give the outfit a little bit of sexiness. I found a Nordstroms Rack (I love that store) and started hunting for my outfit. I found some cute booties that were perfect and was able to try them on myself. I also found a cream sweater cardigan that was perfect for wearing over a little white top that I also found at the store. No luck on a skirt or tights so went to a couple of other stores. I found the skirt at a Macy's and it was on sale!! It was a darker brown suede mini skirt that had some squares sewed into it and was just so cute and fit perfectly. I also found the nude fishnets tights which I think would look sexy but also got some sheer cream hose that would be a bit more conservative. I also stopped by the makeup counter and picked up some new lipstick, a concealer, and powder (recommendations from the makeover I just had). It was after noon and I was a little hungry so stopped for a salad before heading to a Walmart to get a few things I needed to make sure I was clean for what I thought was going to happen tonight with Tim.

I got back to the hotel around 2pm and laid out all of my new purchases to make sure I had everything I needed for tonight. If things went as I wanted, I wanted to wear some lingerie I had for Tim so I pulled out the cream corset, panties and stockings that I already owned. Satisfied that I had everything I need, I started getting myself ready. I was really self-conscious about being totally clean for Tim so I proceeded with giving myself several "internal" cleanings. Once totally clean I took a long bath and shaved my legs and every other area so make sure I was smooth and as feminine as possible. After my bath I shaved my face very closely and sat down to start with my makeup.

I learned so much from the makeover the previous day and used it to do my makeup, however I did not go as heavy as the makeover since I was getting ready for a dinner vs a night out. I think I did a pretty good job and was happy with the outcome. I pulled out both of the wigs and tried them on, both looked so good that I was having a hard time decided between the blonde and auburn. However, since Tim was with me last night and my previous wig was auburn, I decided to stick with that color. I got a text from Tim saying he was excited to see me tonight and was thinking about me, which caused the butterflies to start in my stomach. It was almost 6 o'clock and I felt the day was flying by, how do regular girls do this all time, I wanted to know!!

I put on my waist nipper which had a built-in bra that gave me some boobs and slipped into some tight panties that are not very sexy but hide myself rather well. I needed to decide on which hose to wear and thought the fishnets would be a nice treat for Tim to look at and I know that they are very comfy to wear. I slipped them on my legs and up my waist, then the white top and suede skirt. I put on the booties and just love how they looked with the tights. They were a light brown suede with a 2.5-inch block heel and came up just above the ankle. I put on some of the jewelry I had and added my cardigan and I was ready for Tim to show up. I got a text from Tim which said he was down in the lobby and I told him to come up to my room for a quick drink (I had some wine leftover). He knocked on the door and was looking very cute, as I let him in, he gave me a quick kiss and told me I look fabulous and he loved my outfit. I did a quick spin and I said it is mostly a new outfit that I just got for this special date with him. He said I look so pretty in it and just like a woman which is such a turn on for me to hear. I poured us glasses of wine and we sat down on the bed. He told me that he could not stop thinking about me and got no work done at all today because he was looking forward to seeing me again. He asked how I was doing and feeling about last night. I told him I was doing good and said I really enjoyed last night. I said it was a big step for me but that I was amazed at how it made me feel so feminine, and also how good it felt to give him so much pleasure.

He smiled at me and told me how amazing that was for him and that he was so honored to be my first blowjob. He said it was the best blowjob he ever had and said he was getting excited just thinking about it. I reached over and felt him and he was not lying, he was getting hard again.

"Oh my you are getting hard again!"

Tim said, "I am so sorry but I cannot help it, you are looking so good right now and we started talking about the blowjob you gave me and I am just so excited for you."

"Well, we can't go to dinner with you in that condition can we?"

I had him stand in front of me and his pants and underwear were down in a flash and I was once again staring at a nice cock in front of me. I noticed he had trimmed his hair a lot and shaved his balls so he had a pretty smooth cock now. I grabbed his cock and quickly had it in my mouth and started bobbing up and down on it, he moaned loudly as it first went in and said "oh my goodness that feels so good and you look so hot with my cock in your mouth."

He must have been so turned on already because he did not last for more than 2 minutes and I felt him tense up and start to pump his cum into me. I was somewhat ready for this and pulled him to the front of my mouth as his orgasm slowed down and I kept him in my mouth and made sure every drop of cum was out of his cock before letting it fall out. I was making sure I did not get any on my new outfit so swallowed it all down and smiled at him and said, "are you all better now?"

He laughed and stood me up and gave me a big kiss and told me I was the most amazing girl he has ever been with. That almost made me get hard and have to cum!

I excused myself to touch up my makeup and put on new lipstick and gloss. I looked in the mirror and smiled to myself, I had just given my second blowjob and it felt like I was supposed to be doing it to make my guy happy and most of all I just felt very feminine and almost comfortable.

I came out of the bathroom and told Tim I was ready to go. Tim said, "Jaime that was so wonderful but you have pleased me twice and I want to return the favor."

"Thanks Tim that is so sweet and I am hoping you will get the chance tonight after dinner, besides you may not realize it but I was very pleased to be able to do that with a guy as nice as you." I gave him a little kiss and said, "I am getting hungry."

I was not nearly as nervous going out in public having a guy with me and I did not stick out like a guy in drag which I was fearing. I think it helped that I had on a cute outfit and not something super sexy which was more likely for a crossdresser. Dinner was so nice in a small restaurant and Tim was such a gentleman the whole time. We talked all through dinner and it was just like a guy and girl getting to know each other. He did ask about what I was planning to do for the future, and that was where it was a mystery to me. I loved being a girl but also liked my boy life, and was not ready for going further than playing a girl once in a while. He understood and told me he would like to be my boyfriend but understood that it would be under my terms as far as availability. After dinner we took a walk holding hands and just enjoying the evening, and then I asked if he was ready to go back to my hotel. He turned to me and kissed me deeply and I felt him getting hard again on my leg, and he said, "do you think I am ready?"

"Well, it does feel that way!"

He raced back to the hotel, I had to tell him to slow down since he was so excited. To tell you the truth I was as well. Once in the room he started kissing me deeply and touching my breasts and butt. I was returning the kisses and was getting very hot myself and let him know that I wanted to feel him inside me. I pulled back and told him to get underdressed and I would be back in a minute.

I went to the bathroom where I had my lingerie and quickly took off my outfit and got into the corset, panties and stockings. I reapplied my lip stick and put on some strappy heels and was ready to go out. Tim was naked and was fully erect as I came from the bathroom, and he gasped when he saw me.

"You are so beautiful and look so amazing," he said.

"Thank you Tim.....I am ready for you"

I had some lubrication ready on the nightstand and made sure to put a nice amount on his now familiar cock. As I was about to do the same for my bottom Tim said to wait as he wanted to have some fun with me first. I laid down on my back and lifted my legs up to my head, and Tim went down on me and started licking my hole. A girl had done this to me one time before, but Tim sure did know what he was doing, it felt amazing to have his tongue up in me and tasting me just like a girl. After I few minutes I was ready for the real thing to happen.

I got up on my hands and knees on the edge of the bed and Tim stood behind me, he reached for some lubricant and applied some to my waiting hole inserting a finger in me which caused me to shutter. Then I felt his warm cock head resting on my entrance and I got another wave of anxiety. Even though I have used a dildo on myself many times (and really enjoyed it) much like giving my first blowjob this was a big step. I was about to be penetrated by a guy and would forever be different. Was I now gay or bi, or trans? Would I only want to have sex like this from now on? Should I become a girl full time and go on hormones? Too many questions were flashing in my mind when I felt Tim's head enter into my bottom and felt how warm and hard it was. I let out a little gasp as the head fully entered me and Tim paused to ask if I was ok.

"Oh my gosh, yes, that feels so good, hang on"

Tim paused for a bit while I relaxed and then I asked him to keep going. As he filled me up I was overwhelmed at the feel of a real cock inside me. It was so warm and felt amazing, and I could feel it going in deeper and deeper until I felt his balls on me. I was being fucked and I was in ecstasy. Tim pulled back slowly and began pumping into me slowly. It felt so good and any anxiety I felt was washed away from the feelings of being taken just like a real woman. As Tim continued thrusting into me, he was holding his hands on my hips and then feeling my legs, which was amazing. As he continued, I kept on moaning and saying "oh my gosh I'm a girl, I'm a girl" as Tim was saying "you are so beautiful".

I lifted myself and turned to Tim's face while he was still in me and started kissing him desperately. "Fuck me, fuck me, make me a girl" I yelled.

Tim continued pumping into me and feeling my legs and hips with his hands. It was feeling so good and I was fully erect but the pleasure was all from the inside. I felt him so deep in me and I started to sense my orgasm building quickly. It was starting from the inside of me verses my cock area and was overwhelming. I started matching Tim pumping into me by backing into him and the intensity picked up.

I was yelling, "I am going to cum, I am going to cum, I am going to cum"

I let out a very long moan as I felt my orgasm start and then Tim thrust into me all the way and I felt him get bigger and bigger. His cock started pumping and I felt the first cum shot go deep into me. I felt my eyes roll back as my orgasm was at full intensity. I was overcome with pleasure and was just repeating, "oh fuck, oh fuck, oh fuck" over and over as Tim continued pumping his cum deep into me.

Just as Tim's cock stopped pulsing, mine let out big streams of cum over and over. I was in total bliss and I was on all fours on the bed waiting for the intensity of feelings to subside. After I came back to earth, I laid on my side with my legs together and felt Tim's cum coming out of my hole. I don't know why but that felt so feminine to me. Tim went to the bathroom to get a warm wet towel and helped clean me up (and all the cum on the bed). I thought to myself how sweet it was of him to do that for me. When he was done, I got to my feet and put my arms around Tims neck and kissed him very deeply, and then told him, "I think I want to be a girl!"